Françoise Zammattio

The synthesis of 3-trimethylsilyl-4-dimethyl(phenyl)silylbut-3-en-2-one, a β-functionalised Michael acceptor

Abstract The title compound 3 has been prepared by silyl-cupration of trimethylsilylacetylene followed by acetylation. The phenyldimethylsilyl group can be removed selectively in a three-step procedure to give 3-trimethylsilylbut-3-ene-2-one 1b. The enone 3 and cyclohexanone can be used in an annelation reaction to make 5-dimethyl(phenyl)silylbicyclo[4.4.0]decan-3-one 20 and hence to make 2-vinylcyclohexylacetic acid 23.

Polymer-Supported Organotin Reagents for Regioselective Halogenation of Aromatic Amines

[reaction: see text] Polymer-supported triorganotin halides were used in the halogenation reaction of aromatic amines. Treatment of aromatic amines with n-butyllithium and polymer-supported organotin halides gave the corresponding polymer-bound N-triorganostannylamines, which by treatment with bromine or iodine monochloride gave the para-halogenated aromatic amines with high yields and high selectivities. The polymer-supported organotin halides reagents regenerated during the course of the halogenation reaction can be reused without loss of efficiency. The presence of tin residues in halogenated aromatic amines was also investigated and evaluated at under 20 ppm after three runs.

The promoting effect of pyridine ligands in the Pd-catalysed Heck–Matsuda reaction

An efficient Pd-catalyzed arylation reaction of challenging acyclic olefins, in the presence of an organic ligand, has been disclosed. Commercially available cheap pyridine-based ligands are able to promote good to excellent yields for poorly efficient Heck–Matsuda arylation reactions of several allylic alcohols. A wide range of electronically different arenediazonium salts bearing either electron-releasing or withdrawing groups have been used allowing the synthesis of a range of β-aryl-methoxy-lactols. The catalytic system has been optimised, along with the reaction conditions, in order to achieve remarkable yields in less than 1 h.